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. Author manuscript; available in PMC: 2017 Jul 7.
Published in final edited form as: Org Biomol Chem. 2016 May 24;14(25):5894–5913. doi: 10.1039/c6ob00878j

Scheme 9.

Scheme 9

Rugulovasines A (11a) and B (11b). Reagents and conditions: (a) furanyl stannane 97, Pd(PPh3)4, PhMe, K2CO3, reflux, 1 h then (Boc)2O, DMAP, Et3N, 94%; (b) DIBAL-H, −78 °C to room temperature, then SiO2, 71%; (c) CBz-OSuc, Et3N, DMF, room temperature, 26 h; (d) NaH, MeI, DMF, 85% (2 steps); (e) Cs2CO3, MeOH; (f) H2, Pd/C, MeOH-THF, 11a:11b (2:1), 74% (2 steps).